Aporphine and phenanthrene alkaloids with antioxidant activity from the roots of Stephania tetrandra

Wang, Renzhong; Zhou, Jie; Shi, Guo-Ru; Liu, Yanfei; Yu, De‐Quan

doi:10.1016/j.fitote.2020.104551

Cited by 22 publications

(8 citation statements)

References 22 publications

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“…The absolute configuration at 6a was deduced as R because of the negative sign of specific optical rotation and electronic circular dichroism (ECD) Cotton effects. 28 Furthermore, the calculated ECD curve for the absolute configuration of 6aR was consistent with the experimental curve (Figure S20). Therefore, compound 3 was identified as (R)-1,2-methylenedioxy-9methoxy-11-hydroxyaporphine.…”

Section: ■ Results and Discussionsupporting

confidence: 78%

Bioactive Isoquinoline Alkaloids with Diverse Skeletons from Fissistigma polyanthum

Jiang,

Liu,

Liu

et al. 2023

J. Nat. Prod.

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Six new isoquinoline alkaloids, including aporphine alkaloids (2, 3, 9, and 10), a benzylisoquinoline alkaloid (13), and a protoberberine alkaloid (17), were isolated from the roots of Fissistigma polyanthum, along with a new furanone (20) and 13 known isoquinoline alkaloids (1, 4−8, 11, 12, 14−16, 18, and 19). The structures of the new compounds were elucidated by the analysis of spectroscopic data. Compounds 1 and 2 are rare oxalylfused dehydroaporphine alkaloids. Compound 12 presented the most potent dual-target activities on AChE inhibition and Aβ aggregation inhibition, while compounds 13 and 19 simultaneously exhibited discernible AChE and BChE inhibitions with antioxidant activities. The activity results indicate that F. polyanthum alkaloids have a potential of inhibition and prevention of Alzheimer's disease mainly through both ChEs and β-amyloid pathways in addition to antioxidant activity.

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Section: ■ Results and Discussionsupporting

confidence: 78%

Bioactive Isoquinoline Alkaloids with Diverse Skeletons from Fissistigma polyanthum

Jiang,

Liu,

Liu

et al. 2023

J. Nat. Prod.

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show abstract

“…The results showed the presence of various chemical compounds, such as fatty acids, terpenes, alkaloids, coumarines, and flavonoids. These classes are already known by their antioxidant abilities [78,79], and thus, they may explain the present activity. The analyzed peptides showed in Table 2 can also explain in part the antioxidant activity [80][81][82].…”

Section: Antioxidant Activitiesmentioning

confidence: 74%

HR-LCMS-Based Metabolite Profiling, Antioxidant, and Anticancer Properties of Teucrium polium L. Methanolic Extract: Computational and In Vitro Study

et al. 2020

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In this study, we investigate the phytochemical profile, anticancer, and antioxidant activities of Teucrium polium methanolic extract using both in vitro and in silico approaches. The results showed the identification of 29 phytochemical compounds belonging to 13 classes of compounds and 20 tripeptides using High Resolution-Liquid Chromatography Mass Spectrometry (HR-LCMS). 13R-hydroxy-9E,11Z octadecadienoic acid, dihydrosamidin, valtratum, and cepharantine were the main compounds identified. The tested extract showed promising antioxidant activities (ABTS-IC50 = 0.042 mg/mL; 1,1-diphenyl-2-picrylhydrazyl (DPPH)-IC50 = 0.087 mg/mL, β-carotene-IC50 = 0.101 mg/mL and FRAP-IC50 = 0.292 mg/mL). Using both malignant Walker 256/B and MatLyLu cell lines, T. polium methanolic extract showed a dose/time-dependent antitumor activity. The molecular docking approach revealed that most of the identified molecules were specifically binding with human peroxiredoxin 5, human androgen, and human progesterone receptors with high binding affinity scores. The obtained results confirmed that T. polium is a rich source of bioactive molecules with antioxidant and antitumor potential.

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“…The absolute configuration of C‐6a was assigned as S by comparison of the ECD spectrum (Figure S3.9, Supporting Information) with that of glaucine. [ 23 ]…”

Section: Resultsmentioning

confidence: 99%

Alkaloid Dimers Isolated from Thalictrum baicalense Have Antitumor Activities

et al. 2022

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A pair of heterodimeric isoquinoline alkaloid enantiomers, (±) thaliberberine A, five new thalifaberine-type aporphine-benzylisoquinoline (ABI) alkaloids, thalicultratines M-Q, and thirteen known analogues were isolated from the roots of Thalictrum baicalense Turcz. ex Ledeb. The structures were determined by extensive spectroscopic methods and ECD calculations. Thaliberberine A featuring a novel carbon skeleton coupled by two different classes of isoquinoline alkaloids, protoberberine and phthalidoisoquinoline, represents the first natural product with the berberine skeleton substituted at C-6. Plausible biosynthetic routes of 1 are proposed. All isolated alkaloids were screened for their antiproliferative effects in vitro against HCT116, Caco-2, and HepG-2 cancer cell lines. The most active ABI alkaloid, thalifaronine (7) induced G0/G1 cell cycle arrest and apoptosis. Compound 7 effectively inhibited the colony formation and tumor growth of HCT116 cells in xenografts. The thalifaberine-type ABI dimers represent a group of compounds with antitumor activity. The spectroscopic characteristics of thalifaberine-type ABI dimers were also analyzed.

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Aporphine and phenanthrene alkaloids with antioxidant activity from the roots of Stephania tetrandra

Cited by 22 publications

References 22 publications

Bioactive Isoquinoline Alkaloids with Diverse Skeletons from Fissistigma polyanthum

Bioactive Isoquinoline Alkaloids with Diverse Skeletons from Fissistigma polyanthum

HR-LCMS-Based Metabolite Profiling, Antioxidant, and Anticancer Properties of Teucrium polium L. Methanolic Extract: Computational and In Vitro Study

Alkaloid Dimers Isolated from Thalictrum baicalense Have Antitumor Activities

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